When Jake arrives late for work, Captain Holt decides to shadow him. However, the arrest they make proves complicated. Meanwhile, a psychic friend of Gina's gets inside Charles' head.
With a backlog of unsolved cases, Jake finds himself in a slump. Meanwhile, Amy is put in charge of the Junior Police Program for at risk kids, but her efforts to inspire them fall flat.
Jake meets an attractive Medical Examiner, but their relationship slows down her work, much to his colleagues' annoyance. Meanwhile, Amy desperately tries to impress Holt.
Jake makes a foolish bet with Holt that he can steal his Medal of Valor before Halloween is over, while Amy is forced to wear a costume while undercover with Charles.
Jake is horrified when his hero, Jimmy Brogan, a crime writer, accompanies him on the job, and threatens to quote him in a damning article. Meanwhile, Rosa has to work on her attitude in court.
Jake's favorite pizza place burns down and he is determined to prove the owner was not responsible. Meanwhile, Amy is jealous of Rosa's being offered a promotion, and Terry and Gina have to hire a new IT specialist.
When Holt receives death threats, he surprisingly puts Jake in charge of his security. Meanwhile, Terry undergoes a psych evaluation, and Amy tries to make the perfect holiday card for Holt.